Odd-even alternation in tautomeric porous organic cages with eceptional chemical stability
| Title | Odd-even alternation in tautomeric porous organic cages with eceptional chemical stability |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Bera, S, Basu, A, Tothadi, S, Garai, B, Banerjee, S, Vanka, K, Banerjee, R |
| Journal | Angewandte Chemie-International Edition |
| Volume | 56 |
| Issue | 8 |
| Pagination | 2123-2126 |
| Date Published | FEB |
| Type of Article | Article |
| Abstract | Amine-linked (C-NH) porous organic cages (POCs) are preferred over the imine-linked (C= N) POCs owing to their enhanced chemical stability. In general, aminelinked cages, obtained by the reduction of corresponding imines, are not shape-persistent in the crystalline form. Moreover, they require multistep synthesis. Herein, a one-pot synthesis of four new amine-linked organic cages by the reaction of 1,3,5-triformylphloroglucinol (Tp) with different analogues of alkanediamine is reported. The POCs resulting from the odd diamine (having an odd number of -CH2 groups) is conformationally eclipsed, while the POCs constructed from even diamines adopt a gauche conformation. This odd-even alternation in the conformation of POCs has been supported by computational calculations. The synthetic strategy hinges on the concept of Schiff base condensation reaction followed by keto-enol tautomerization. This mechanism is the key for the exceptional chemical stability of cages and facilitates their resistance towards acids and bases. |
| DOI | 10.1002/anie.201611260 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 12.102 |
Divison category:
Physical and Materials Chemistry